ChemFOnt: Showing chemical card for 3-Oxohexadecanoyl-CoA (CFc000002738)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:41 UTC

Chemfont ID

CFc000002738

Molecule Identification

Common Name

3-Oxohexadecanoyl-CoA

Definition

3-Oxohexadecanoyl-CoA has a role in the synthesis and oxidation of fatty acid. It is involved in the pathway, fatty acid elongation in mitochondria. In this pathway Acetyl-CoA is acted upon by the enzyme, acetyl-CoA C-acyltransferase to produce 3-Oxohexadecanoyl-CoA. Since coenzyme A is chemically a thiol, it can react with carboxylic acids to form thioesters, thus functioning as an acyl group carrier. It assists in transferring fatty acids from the cytoplasm to the mitochondria. A molecule of coenzyme A carrying an acetyl group is also referred to as acetyl-CoA. When it is not attached to an acyl group it is usually referred to as 'CoASH' or 'HSCoA'.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Ketopalmitoleoyl-CoA	HMDB
3-Ketopalmitoleoyl-coenzyme A	HMDB
3-Ketopalmitoyl-CoA	HMDB
3-Ketopalmitoyl-coenzyme A	HMDB
3-oxo-cis-9-Hexadecenoyl-CoA	HMDB
3-oxo-cis-9-Hexadecenoyl-coenzyme A	HMDB
3-Oxohexadec-9Z-enoyl-CoA	HMDB
3-Oxohexadec-9Z-enoyl-coenzyme A	HMDB
3-Oxohexadec-cis-9-enoyl-CoA	HMDB
3-Oxohexadec-cis-9-enoyl-coenzyme A	HMDB
3-Oxopalmitoleoyl-CoA	HMDB
3-Oxopalmitoleoyl-coenzyme A	HMDB
3-Oxopalmitoyl-CoA	HMDB
3-Oxopalmitoyl-coenzyme A	HMDB

Chemical Formula

C₃₇H₆₄N₇O₁₈P₃S

Average Molecular Weight

1019.926

Monoisotopic Molecular Weight

1019.324138505

IUPAC Name

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-oxohexadecanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

Traditional Name

[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-oxohexadecanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid

CAS Registry Number

34619-89-1

SMILES

CCCCCCCCCCCCCC(=O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12

InChI Identifier

InChI=1S/C37H64N7O18P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-25(45)20-28(47)66-19-18-39-27(46)16-17-40-35(50)32(49)37(2,3)22-59-65(56,57)62-64(54,55)58-21-26-31(61-63(51,52)53)30(48)36(60-26)44-24-43-29-33(38)41-23-42-34(29)44/h23-24,26,30-32,36,48-49H,4-22H2,1-3H3,(H,39,46)(H,40,50)(H,54,55)(H,56,57)(H2,38,41,42)(H2,51,52,53)/t26-,30-,31-,32?,36-/m1/s1

InChI Key

NQMPLXPCRJOSHL-TZIIWEFPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain 3-oxoacyl coas. These are organic compounds containing a coenzyme A derivative, which is 3-oxo acylated long aliphatic chain of 13 to 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

Long-chain 3-oxoacyl CoAs

Alternative Parents

Substituents

Coenzyme a or derivatives
Purine ribonucleoside 3',5'-bisphosphate
Purine ribonucleoside bisphosphate
Purine ribonucleoside diphosphate
Ribonucleoside 3'-phosphate
Pentose phosphate
Pentose-5-phosphate
Beta amino acid or derivatives
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Pentose monosaccharide
Imidazopyrimidine
Purine
Monoalkyl phosphate
Aminopyrimidine
1,3-dicarbonyl compound
Imidolactam
Monosaccharide
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Pyrimidine
Alkyl phosphate
Fatty amide
Phosphoric acid ester
Tetrahydrofuran
Imidazole
Azole
Heteroaromatic compound
Carbothioic s-ester
Secondary alcohol
Ketone
Thiocarboxylic acid ester
Carboxamide group
Secondary carboxylic acid amide
Amino acid or derivatives
Sulfenyl compound
Thiocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid derivative
Organosulfur compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Primary amine
Organopnictogen compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Peroxisome (HMDB: HMDB0006402)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0006402)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0006402)

Source

Endogenous

Endogenous (HMDB: HMDB0006402)

Animal

Animal (HMDB: HMDB0006402)

Exogenous

Food

Food (HMDB: HMDB0006402)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0006402)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0006402)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0006402)
Fatty Acid Metabolism (PathBank: SMP0063589)
Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty Acids (PathBank: SMP0087267)
Fatty Acid Elongation In Mitochondria (PathBank: SMP0087294)
Fatty Acid Metabolism (PathBank: SMP0002361)
Fatty Acid Elongation In Mitochondria (PathBank: SMP0002368)
Fatty Acid Elongation (PathBank: SMP0121069)
Fatty Acid Elongation In Mitochondria (PathBank: SMP0063612)
Fatty Acid Oxidation (Palmitate) (PathBank: SMP0121352)

Disease pathway

Very-Long-Chain Acyl-CoA Dehydrogenase Deficiency (VLCAD) (PathBank: SMP0120824)
Carnitine Palmitoyl Transferase Deficiency II (PathBank: SMP0120825)
Long-Chain-3-Hydroxyacyl-CoA Dehydrogenase Deficiency (LCHAD) (PathBank: SMP0120827)
Ethylmalonic Encephalopathy (HMDB: HMDB0006402)
Trifunctional Protein Deficiency (PathBank: SMP0120609)
Ethylmalonic Encephalopathy (PathBank: SMP0120696)
Carnitine Palmitoyl Transferase Deficiency I (PathBank: SMP0120822)
Long Chain Acyl-CoA Dehydrogenase Deficiency (LCAD) (PathBank: SMP0120604)
Medium Chain Acyl-CoA Dehydrogenase Deficiency (MCAD) (PathBank: SMP0120607)
Short-Chain Acyl-CoA Dehydrogenase Deficiency (SCAD Deficiency) (PathBank: SMP0120740)
Glutaric Aciduria Type I (PathBank: SMP0000185)

Lipid metabolism pathway (HMDB: HMDB0006402)

Cellular process

Cell signaling (HMDB: HMDB0006402)

Biochemical process

Lipid transport (HMDB: HMDB0006402)

Role

Biological role

Energy source (HMDB: HMDB0006402)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0006402)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.01 g/L	ALOGPS
logP	1.96	ALOGPS
logP	-1.2	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	0.83	ChemAxon
pKa (Strongest Basic)	4.95	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	380.7 Å²	ChemAxon
Rotatable Bond Count	34	ChemAxon
Refractivity	237.34 m³·mol⁻¹	ChemAxon
Polarizability	99.31 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon